TY - JOUR AU - Li, Kaicheng; Gao, Jianmin TI - Iminoboronate-Mediated Peptide Cyclization with Lysine Homologues SN - 0936-5214 SN - 1437-2096 PY - 2017 JO - Synlett JF - Synlett LA - EN VL - 28 IS - 15 SP - 1913 EP - 1916 ET - 2017/07/05 DA - 2017/09/05 KW - peptide cyclization KW - reversible KW - iminoboronate KW - 2-APBA KW - Dap KW - pH AB - Cyclic peptides are attracting attention of medicinal chemists due to their increased stability in biological milieu as well as improved target binding affinities. Our laboratory has recently reported a powerful cyclization strategy that takes advantage of the spontaneous and reversible conjugation of lysine and a designed amino acid AB3 to give iminoboronates. Herein we report that Dap, a short chain homologue of lysine, displays significantly higher propensity to form imino­boronates and consequently improves the efficiency of peptide cyclization. Importantly, the preferential conjugation of AB3 to Dap allows a facile synthesis of cyclic peptides with free lysine residues. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1590795 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1590795 ER -